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Triphenylene

Names
Preferred IUPAC name Triphenylene
Other names Benzophenanthrene 9,10-Benzophenanthrene 1,2,3,4-Dibenzonaphthalene Isochrysene
Identifiers
CAS Number	217-59-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33080
ChEMBL	ChEMBL1797416
ChemSpider	8816
ECHA InfoCard	100.005.385
EC Number	205-922-9
KEGG	C19541
MeSH	C009590
PubChem CID	9170
UNII	18WX3373I0
CompTox Dashboard (EPA)	DTXSID9059757
InChI InChI=1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12HKey: SLGBZMMZGDRARJ-UHFFFAOYSA-N InChI=1/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
SMILES c1(cccc3)c3c(cccc4)c4c2c1cccc2
Properties
Chemical formula	C18H12
Molar mass	228.294 g·mol
Appearance	white
Density	1.308 g/cm
Melting point	198 °C; 388 °F; 471 K
Boiling point	438 °C; 820 °F; 711 K
Magnetic susceptibility (χ)	-156.6·10 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Triphenylene is an organic compound with the formula (C₆H₄)₃. A flat polycyclic aromatic hydrocarbon (PAH), it consists of four fused benzene rings. Triphenylene has delocalized 18-π-electron systems based on a planar structure, corresponding to the symmetry group D_3h. It is a white or colorless solid.

Preparation

Triphenylene can be isolated from coal tar. It can also be synthesized in various ways. One method is trimerization of benzyne. Another method involves trapping benzyne with a biphenyl derivative.

Properties

Triphenylene is more resonance stable than its isomers chrysene, benzanthracene, benzophenanthrene, and tetracene. For this reason triphenylene resists hydrogenation.

As a disc-shaped, planar molecule, triphenylene has attracted attention as the core of discotic mesogen in liquid crystalline materials.

References

1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 209. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. Ahmed, F. R.; Trotter, J. (1963). "The crystal structure of triphenylene". Acta Crystallographica. 16 (6): 503–508. Bibcode:1963AcCry..16..503A. doi:10.1107/S0365110X63001365.
3. Heaney, H.; Millar, I. T. (1960). "Triphenylene". Organic Syntheses. 40: 105. doi:10.15227/orgsyn.040.0105.
4. Katie A. Spence, Milauni M. Mehta, Neil K. Garg (2022). "Synthesis of Triphenylene via the Palladium–Catalyzed Annulation of Benzyne". Organic Syntheses. 99: 174–189. doi:10.15227/orgsyn.099.0174. S2CID 250383238.{{cite journal}}: CS1 maint: multiple names: authors list (link)
5. Kofman, V.; Sarre, P.J.; Hibbins, R.E.; ten Kate, I.L.; Linnartz, H. (2017). "Laboratory spectroscopy and astronomical significance of the fully-benzenoid PAH triphenylene and its cation". Molecular Astrophysics. 7: 19–26. Bibcode:2017MolAs...7...19K. doi:10.1016/j.molap.2017.04.002. hdl:1887/58655. S2CID 67834616.
6. Janietz, Dietmar (2001), "Liquid Crystals at Interfaces", Handbook of Surfaces and Interfaces of Materials, Elsevier, pp. 436–437, doi:10.1016/b978-012513910-6/50014-1, ISBN 978-0-12-513910-6, retrieved 2020-08-23

External links

• Polycyclic Aromatic Hydrocarbon Structure Index Archived 2008-02-15 at the Wayback Machine

• Polycyclic aromatic hydrocarbons
• Tetracyclic compounds